


Extra Help

by sassquire



Category: The Venture Bros
Genre: Dry Humping, F/M, First Time, Strip Tease, dean is 18 obvs, dean is a dork, dean is a nerd, humping, no sirena FUCK SIRENA, semi-rough sex, takes place in season 7, this entire fic is just poor impulse control and horniness
Language: English
Status: Completed
Published: 2019-03-12
Updated: 2019-03-12
Packaged: 2019-11-15 22:04:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,245
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18081764
Author URL: https://archiveofourown.org/users/sassquire/pseuds/sassquire
Summary: “I-I’ll be honest--” Dean rose a hand and rubbed the back of his neck, grinning awkwardly. “--...I don’t really have any idea what’s going on in this class…”His hand lowered, and he looked at you sheepishly. “Do you think we could maybe-- ...study? Together? Tonight?”





	Extra Help

“--...and that leaves us with the square root of forty five over the square root of twelve. Does everyone see what I did there?” The professor announced, putting his stub of chalk down onto the small metal railing at the bottom of the board.  
  
He looked out onto the sea of students, some scribbling away in their notebooks, while others stared blankly at the board in a half-awake stupor.  
  
Silence.  
  
Their instructor sighed, and his shoulders faintly slouched. “Don’t you guys drink coffee in the morning? I know it’s 8 in the morning, but come on, _I’m_ wide awake up here…..--”  
  
You sighed and leaned to the left in your seat, resting your chin in your hand as your other one twirled a mechanical pencil around. You got these ‘are you guys even paying attention’ lectures at least twice a month.  
  
At least it ate up class time.  
  
As you zoned out and lightly tapped your pencil against your notebook, you failed to notice your classmate next to you having his gaze on your notes.  
  
He was slowly tapping the bud of his pen against his own emptier-by-comparison pages, and had his features subtly twisted in anxious frustration.  
  
  
_Dean was good at math._ He always understood the equations and practice problems his learning bed gave him, but… He only vaguely knew what was going on in this class.  
  
It was _algebra,_ yeah, but all of these methods, techniques and rules he was expected to already know...he had _never seen before!_ _  
_ _  
_ A soft, aggravated groan left his puckered lips, and his green gaze drifted down to his own abandoned notes. Of course, his learning bed was the scraps and leftovers of what his father was taught in the 60’s, none of it was even _relevant_ anymore!  
  
He couldn’t even be bothered to _update it_ for them before chucking them into it.  
  
Dean sighed softly, and gently hunched forwards. Alright, no.. getting worked up over things he couldn’t change was pointless… He couldn’t change how he was raised, but he _could_ change his math skills.  
  
His gaze returned to the blackboard, and Dean’s brows twitched upwards in dread.  
  
_He didn’t even know what questions to ask._  
  
Which, of course, brought his thoughts back to the student beside him, with her notebook filled to the brim with numbers and equations.  
  
You looked like you knew what you were doing. And you were... _right there,_ so…  
  
From his peripherals, Dean watched you lean back in your seat and cross a leg over the other as you blankly gazed at the professor carried on through his lecture. You tapped the tip of your pencil to your desk in a quiet, random rhythm which you followed by subtly wiggling your leg.  
  
He didn’t notice it, but he found himself paying more attention to your subtle, bored movements than whatever the instructor was saying. He faded into a blur in the background as, still from the corner of his vision, Dean was almost in a trance as he unintentionally studied your subtle movements.  
  
A small, small smile graced his lips, and--  
  
The sound of chairs scraping against the floor and textbooks being dropped into bookbags suddenly cascaded into the air, and the rust-haired Venture snapped back into reality with a slight start. He looked around, watching the class rise from their seats and trickle out of the doors.  
  
How-- ...how long had he been spaced out like that?  
  
“Test is on Thursday, no retakes.” The professor muttered, only half paying attention. He was focusing on his laptop, most likely updating grades.  
  
Dean felt a wave of anxiety wash over him. He was in _no way_ ready for this test. Or, hell, even tests in general! Dean was barely even aware of the concept before applying to college.  
  
Entrance exams? Tests? Final exams, midterm exams…  
  
Not to mention the thrilling adventure of Dean having to figure out what the hell _MLA format_ was…  
  
He noticed you putting away your notebooks into your bag from the corner of his vision, and an idea sprang to him. A bit of a scary idea, as it involved approaching you, but...you were his only chance.  
  
You had just begun to close and secure your bag when you heard the boy sitting next to you speak up.  
  
“H-Hey, you-- know what you’re doing in this class, right?” The freckled boy spoke up, eyeing you with faintly knitted brows.  
  
After pausing for a moment, you looked up from your bag and met his gaze. Like, looked waaay up--  
  
Good god he was tall.  
  
The question actually threw you for a loop for a second, though you answered anyway. “I mean-- I _hope_ I do?”  
  
  
Dean lifted up his book bag and smiled lightly down at you, though it was tinged with nervousness. “I-I’ll be honest--” He rose a hand and rubbed the back of his neck, grinning awkwardly. “--...I don’t really have any idea what’s going on in here…”  
  
His hand lowered, and he looked at you sheepishly. “Do you think we could maybe-- ...study? Together? Tonight?”  
  
Dean’s cheeks only pinkened. It really sounded like he was asking you out, or something…  
  
Not that he wouldn’t be opposed to that! You were..pretty cute, but that wasn’t what he was doing at all...he just wanted to pass the class!  
  
There’s a pause, and a light turned on in Dean’s eyes as they widened. “I-I’m Dean, by the way. ..V-Venture.”  
  
  
It really did feel like he was asking you out. Maybe he--...was? Though either way…  
  
“Uuuhh-- _...sure_ , yeah, I can help you out.” You replied in a bit of a chipper tone, reaching over and slinging your bag over your shoulder. Honestly, you didn’t mind at all. In fact….you began to like the idea more and more.  
  
The thought of helping another person pass the class-- or at least, this next test, was making you feel a bit warm and fuzzy inside.  
  
At your answer, Dean smiled widely, and let out a noise of relief.  
  
...or...maybe something else was making you feel all warm..  
  
  
“--..r-really? _That’s great!_ Uh- I’m over in dorm building 5-- with Jared. Our names are on the whiteboard..” Dean explained, still sounding a tad sheepish..he couldn’t stop rubbing the back of his neck and messing with his hair shyly.  
  
His heart was thumping a little, and he couldn’t tell if it was from the worry of if you’d help him or not, or...just talking to _you._  
  
  
“Okay! Uh-- how abouttt...tonight at 8?” You asked, adjusting the strap on your shoulder as you smiled up at him. Dean returned it.  
  
  
“Tha--that sounds great! I’ll uh-- I’ll see you there, heh--...” Dean giggled stupidly, and watched with a smile as you stepped past him and sauntered out of the classroom. By the time you left, he was the only one in the room, aside from the professor.  
  
Dean stared at the doorway for a few moments, wearing a small, dumb smile, before the professor broke the silence.  
  
  
“--...you gonna leave, or what? I’ve got another class in 5 minutes.”  
  
  
  
  
You had never actually-- _tutored_ or helped someone study before. So, in the hours leading up to 8 pm, you were leafing over the chapters the upcoming quiz was going to be on and putting together a good summary of things to go over.  
  
Was it overkill? Perhaps, but you were a bit of a nerd and honestly wanted this guy to succeed.  
  
What was his name? _Dean?_  
  
Your attention faded away from the textbook in front of you, and instead traveled back to the small interaction you had with him earlier that day. You remembered his nervous and embarrassed state, how he kept rubbing the back of his neck, his stutters..  
  
He could have just been flustered about having to ask a stranger for help, but...you were getting some...vibes.  
  
Some _‘hey this guy might be into you’_ vibes.  
  
Maybe you should--....do something about that? It was worth a shot… Dean was pretty cute, if you had to be honest. You totally had a thing for ‘lanky, freckled, preppy nerd’ type…..and that emo haircut was growing on you.  
  
You glanced towards your phone, seeing the time.. 7:45. The boy’s dorm was a little bit of a walk, so you went ahead and decided to pack up.  
  
Textbook, notebook, calculator… With your items, you hurried to your door, though your hand paused on the knob.  
  
..  
  
You whirled around and sped over to your bed after placing your stuff down and quickly snatched up a vial of perfume. With heated cheeks you spritzed some on your skin in a rushed fashion, before speed-walking back to your books and opening the door. _Now_ you were off.  
  
Hopefully you weren’t reading anything into this that wasn’t actually there.  
  
  
  
A few minutes after the clock struck 8 pm-- you were walking as _fast_ as you could, you _swore--_ you had hurried down one of the hallways in the boy’s dormitories and finally reached the room marked with a ‘Jared & Dean’ on its whiteboard. _  
_ _  
_ You felt a bit out of place in the boy’s dormitories, but you brought a hand fowards and rapped your knuckles against the wooden door regardless.  
  
...did you look okay? You glanced downwards and tugged your shirt down a bit, exposing a teensy bit more of your chest. As you messed with your clothing, you faintly heard the sound of footsteps approaching the door. And then…--  
  
The door swung open, and you had to look up to see who had answered. There stood the boy from before-- Dean, you remembered his name was, and he beamed once he saw it was you at the door.  
  
“Hey! Uh--....wow, right on time.” The freckled boy remarked, smiling lopsidedly and rubbing the back of his neck. You adjusted the books in your arms and shifted your weight.  
  
  
“Heh-- ...yeah...” You smiled and glanced away, feeling a faint dusting of heat coat your cheeks. ..was it weird that you were on time? Should you have shown up late?  
  
.  
  
..  
  
A good few silent seconds passed, and then you both snapped back to attention and leapt to break silence at the same time.  
  
“W-well, y-you should probably come in--”  
  
“Right, uh-- ready to study?---...”  
  
  
You both paused as you realized you spoke over each other, before the two of you broke out into embarrassed laughter.  
  
Dean felt his heart hammering in his chest-- that was so stupid! Why did he do that?! He turned and led you into his dorm room, his features twisting into an anxious wince once his back was turned.  
  
This was just a tutoring session, but for some reason...Dean felt compelled to impress you, and to make a good impression. His heart exploded into butterflies the moment he opened the door and saw you standing there.  
  
At first, he merely thought it was nerves, worried that he’d look like an idiot for how bad he was at math, but….  
  
...no...this was starting to feel different…  
  
And fortunately for him, though he didn’t know it-- you felt the same.  
  
  
He clicked the door shut, and you glanced around, checking out his room….one side had a bunch of musical and play posters, while the other one had a few..science-y ones? You wondered which side was Dean’s.  
  
Your question was quickly answered when the lanky teen plopped down on the bed closest to the science posters. You paused-- should you...sit on his bed too? You didn’t see any chairs.  
  
Dean seemed to notice this a second after you did, and he looked up at you with slightly widened and embarrassed eyes.  
  
“U-Uh-- ...you can just-- ...sit here-- …..sorry.”  
  
Oh, guess it was fine then. You plopped down in front of him and started placing your books down as Dean mumbled something out. “--....didn’t really….plan this out…”  
  
  
You shrugged lightly, and brushed his concern off. “Eh, no biggie. S’kinda comfier like this, anyway.”  
  
  
Dean softly cleared his throat and shifted in his seat, watching you as you flipped through your textbook to the unit your class was currently on. From the corner of your vision, you noticed his gaze repeatedly flickering away..and then back to your face. There was the faintest, faintest blush dusting his cheeks..  
  
You had to fight to contain a smile. Jesus, was he gonna act that cute for the entire session? How were you going to handle this?!  
  
  
“Alright, so-- ..how stuck are you?” You asked, finally peering up at him with a lopsided smile. Dean seemed a bit taken by surprise at that, and stuttered.  
  
  
“U-Uh-- ..I don’t kn-- _...very?_ I’m completely lost in class-- ...I-I’m not bad at math, I’ve just--..never heard of the techniques and rules the professor talks about!” The Venture boy explained, looking to you with pleading eyes. Please don’t think he’s an idiot, _please_ don’t think he’s an idiot….  
  
  
You paused. “--...wait, really? Where’d you go for high school? Green Meadow?”  
  
  
“N--...no--” Dean muttered, as his brows knitted. His guts twisted a bit.  
  
  
“Townsend Harris?”  
  
  
“N-no, I--” He could barely get a word in.. how was he going to--  
  
  
“--...one of the technical schools? I don’t know anyone from those but like-- we have Common Core, you should have--”  
  
  
“I was kinda-- _....homeschooled,_ so…” Dean quickly interjected, then trailed off, glancing away and wincing. He shrugged his shoulders.  
  
You froze. Way to be an ass. But…  
  
  
“--...oh. That…..explains it. _I think.”_ _  
_  
  
Dean just kept quiet and chewed his lip as his gaze remained to his left, pointedly avoiding yours. He wasn’t going to tell this pretty, smart girl how he was raised in a _compound_ in Colorado Springs and slept in a _learning bed!_ She’d think he was a total nutcase!  
  
  
You remained silent as well for a few moments, as you tried to think of how to continue. Dean looked fairly uncomfortable, and you felt like even more of an asshole.  
  
But then a lightbulb practically went off in your head.  
  
  
“Oh! So, you just need me to catch you up, right?” You chirped, smiling hopefully. Dean’s heart leapt at your reaction-- at least you didn’t question him further on the homeschooling.  
  
  
“I think? But--...wouldn’t that...take awhile? That’s like--” An apologetic, lopsided smile spread across his freckled cheeks. _“--....18 years of math classes…”_ _  
_  
  
Your smile melted away, and Dean felt a stab of guilt. “Yeah, it-- ….would….”  
  
Shit.  
  
  
Again you two fell into silence, and you glanced down at your textbook. Dean said he wasn’t bad at math, right? But….math built on itself, and you’d have to teach him methods upon methods to get to where you were currently at..  
  
  
...how the hell…? Didn’t parents or whatever need to abide by Common Core to homeschool their kids to _avoid_ shit like this?  
  
Well, he passed his entrance exams to get here, so..  
  
“How about I just--...help you to understand _this_ unit? So you can pass the test. At least for now, y’know?”  
  
  
He lit up, and his slouched shoulders rose. “Y-yeah, that works!” Dean chirped, feeling relieved that you thought of a way to help him.  
  
Holy cow, maybe he could actually _pass_ this class!  
  
You smiled, and the two of you soon got to work. It was...a bit of a headache trying to get Dean to wrap his head around the methods described in the textbook, and you couldn’t quite escape the need to backtrack to earlier units-- math absolutely did build upon itself.  
  
But, thankfully, Dean wasn’t kidding...he had a natural knack for this! Thank god, or else you’d be here all night.  
  
..At the same time….you didn’t want to leave him too soon…  
  
As the session went on, the lights switching on in his eyes whenever he finally figured something out, the way he subtly leaned forwards and focused on your face as you tried to explain something...his brows furrowing when he did that, and his lips everrr so slightly puckering when he listened to you just _completely--_ _  
_  
You gulped, and kept your gaze on the textbook as a wave of heat spread onto your cheeks. You were doomed. So doomed.  
  
And if _only you fucking knew_ that when he leaned forwards, and was listening to you-- studying you--...  
  
His guts would twist and wiggle as he noticed your hand gestures, and the tangents you would sometimes go off on when explaining something to him….your stutters, your occasional pauses to brush your hair out of your face…  
  
He just wanted to climb on top of you and---  
  
A wave of heat bloomed onto Dean’s cheeks, and his eyes subtly widened as he brought that thought to a screeching halt. Where the heck did that come from? _Woah!_ _  
_ _  
_ _  
_ “Alright….I think you’re good enough to start doing some of these practice problems.” You muttered, glancing up from the pages to peer at Dean’s curiously red features. Your heart fluttered in your chest a bit...he looked cute with rosey cheeks.  
  
  
“Oh, uh---...okay.” He chirped,shifting in his seat. Dean flipped to the correct unit in his textbook, and his eyes darted around as he looked for a problem to solve. Yet oddly, he was having a hard time focusing.  
  
Honestly, Dean just wanted...to look at _you_ , not this textbook. He was staring down the numbers, but his brain didn’t want to process _any_ of it. He didn’t have the courage to do anything about that, either...you just met him today! There was no way….  
  
Gradually, you began to notice a lack of _problems being solved_ coming from Dean. Was he stuck?  
  
You leaned forwards, causing his heart to hammer in his chest, and your gaze drifted down to his books. Dean chewed his lip and held his breath.  
  
  
“--...you need help?” You asked, still peering downwards. He chewed harder on his lip and shifted.  
  
  
_Did you have to say that while staring at his lap?_  
  
  
“N-no--! Just--.....having trouble focusing.” The freckled boy muttered as his shoulders slouched ever so slightly. He felt a bit like a failure. You put so much time and effort into helping him, and he couldn’t even manage to return the favor.  
  
  
Your brows subtly furrowed as your gaze flickered back up to his features, and the boy felt his skin erupt in warmth. It must have been so obvious…  
  
As you studied him, you felt a bit of warmth bloom onto your own cheeks. You might have been reading into this too much, but…  
  
….maybe he could...use a bit of motivation.  
  
You shifted a bit, and reached around to shrug your jacket off. You did this slowly...you couldn’t really think of a sexy way to take off a jacket, but you tried. Dean’s eyes widened ever so subtly, though he was more confused than anything.  
  
You made your move.  
  
  
“How about this--....for every problem you get right, I’ll--....give you a treat.”  
  
  
Embarrassingly, you didn’t have the courage to just come out and say you’d strip for him, but hopefully Dean got the picture.  
  
He mostly did, and his cheeks erupted into red. “--A--....A-A _treat?”_ He squeaked out in disbelief, feeling his heart jackhammer in his chest. Did he hear that right?  
  
He didn’t unknowingly fall asleep and was having a wet dream all of a sudden, right?!  
  
  
“Mm _hmm,_ so--.....” One of your hands drifted forwards, and you gently pushed the textbook closer to Dean. _“--..hop to it, Dean.”_  
  
  
Hearing his name on your lips pulled a shiver from him, and the boy dove back into his books with a renewed vigor. With his pencil clutched between his fingers, the dorm was filled with the sounds of frantic scribbling and erasing.  
  
Occasionally, his determined and….almost _hungry_ gaze would dart up to yours, just for a second..almost to remind himself what he was working towards.  
  
Thank fucking christ you weren’t wrong about how he felt about you. That would have been an event.  
  
_‘SLAM’._  
  
Dean enthusiastically pressed his pencil into his notebook, and a slightly shaking hand grasped his textbook to flip to the answers page. You tilted your head and twirled a few locks of hair around your finger. Gotta throw him some sort of a bone in the meantime.  
  
His index finger trailed down the page, looking for the exact problem...and then he found it. There was a brief second of pause as he checked his answer.  
  
Then, his nervous though eager eyes locked onto yours.  
  
Your heart thudded in your chest. You didn’t quite know how you were pulling this off so far, but miraculously, it was working. _Now_ you just had to put your money where your mouth was.  
  
Smiling softly (though for all you knew your nervousness was leaking through), your hands snaked down to the hem of your shirt, and you sat up. With agonizing slowness you slipped your shirt upwards, noticing Dean’s eyes widen and the boy stiffen from the corner of your vision.  
  
Once it was blocked when your shirt passed over your face, you heard a sharp inhale.  
  
His gaze darted downwards and was _glued_ to your bra. Dean gulped, and shifted in his seat on his matress. He couldn’t believe this was happening. Your bra was so cute and pretty….and your _boobs--_ _  
_ _  
_ He had to have more of this. You could feel his eyes raking all over your chest and once your shirt was above your head, you swung it around a few times before delicately tossing it towards him, earning a squeak in surprise from the boy.  
  
Dean scrambled to grab your shirt, and completely on impulse, brought it closer to his face and inhaled.  
  
  
A dopey smile spread across his lips as he smelled your perfume. _“O-Oh my god…”_ Dean breathed, sounding absolutely blissful.  
  
  
...wow. This was working way better than you thought it would.  
  
You couldn’t help a proud smirk, and messed with your bra straps as Dean’s eyes traveled over every inch of your exposed chest.  
  
  
“You want more? _Get back to work, Dean.”_ You crowed, leaning back and bracing your palms behind yourself on his mattress. The boy gaped in disbelief, before hurriedly tucking himself back into his work.  
  
Even more so now were his fleeting glances upwards, though they seemed to be focused noticeably lower than your face this time... _  
_ _  
_ As you waited, you went ahead and took off your socks and shoes. ..They didn’t count. There wasn’t anything sexy about taking shoes off. Might as well just get those out of the way.  
  
  
Dean’s heart, meanwhile, was thundering so fast in his chest that he was starting to slightly worry. _How far was this going to go?_  If he got any questions wrong he swore he was going to explode.  
  
The second problem took him a little bit longer ( even though you thought it’d be the opposite ), and after Dean flipped back to the answers page, his eyes met yours again.  
  
_You knew what that meant._  
  
You moved your hands to the front of your pants and began unbuttoning your jeans, making sure the freckled Venture sitting across from you got a nice, good view of what you were doing. His attention was laser focused on the zipper of your pants, and as you slowwwwly zipped it down, you noticed him grabbing a pillow from the corner of your vision and placing it over his lap.  
  
With agonizing slowness your hands drifted up to the waistband of your pants, and Dean was staring so intensely it was as if he was trying to will your pants to come off faster. You could have sworn you heard a _whimper_ from him.  
  
Raising your ass just a bit, you gently began to wriggle out of your jeans and slide them down your legs. Dean sucked in a breath and his eyes popped open to the size of dinner plates as more of your bare skin was revealed to him.  
  
..pulling your pants off without standing up was harder than you thought. Your features scrunched up subtly, and you faintly puckered your lips in concentration. The soft, quiet noises that came from you as you worked to do this as sexily as you could manage made the boy twitch a bit.  
  
The pants finally got passed your ankles, and you gently kicked them off. Dean’s eyes traveled up and down your thighs and along your panties, and his face was so red he roughly resembled a tomato.  
  
It occured to you that very very soon you’d be having to get honest-to-goodness naked infront of this guy, considering you only had your bra and panties remaining at this point.  
  
Judging by the subtle motions of his hips beneath Dean’s conveniently placed pillow, he figured that out as well. Heat rose to your cheeks, and it took everything you had to keep your cool and calm composure.  
  
Were you really doing a strip tease to motivate a guy who you just met today to do his homework?! _Yup!_  
  
A hand rose up to slightly tease your hair as you leaned back, and rose one of your knees to your chest, intentionally giving Dean a view of the crotch of your underwear. He gasped softly, and the faint humping of his pillow intensified.  
  
You lightly swung your thigh left and right, soaking up his reaction. Dean stayed focused on you, and there was a distinct lack of pencil hitting the paper..  
  
...was he waiting for you to make a move?  
  
  
_“.....well?”_ You softly prodded, raising a brow and eyeing him. His gaze finally flickered back up to yours, and he froze...mostly.  
  
  
You hoped that was good enough of a hint for Dean to get back to his problems. That was still the main reason you came here!  
  
Dean certainly got your hint, though….interpreted it _entirely_ differently.  
  
You barely had a second to process what was happening as the freckled boy roughly pushed his textbooks and notebooks off of the mattress, sending them lightly thumping against the carpet of his dorm room.  
  
In the blink of an eye, he was on you, pressing himself against your chest and sending you onto your back against his mattress. Dean’s palms were pressed into the sheets on either side of you, and you felt something stiff poking into your abdomen as he began peppering your neck with kisses.  
  
You froze up completely. That-- that wasn’t what you meant! But--  
  
  
“A-Aaaahh--...D-....Dea--”  
  
  
Honestly….this might be better.  
  
Dean _shuddered_ as he heard your name moaned from your lips, and he melted on top of you-- you didn’t notice it until now, but he had been insanely tense a few moments ago.  
  
Your arms slowly wrapped around his torso as you relaxed into his kisses, and he briefly paused to siiiighhh and breathe in your scent.  
  
He’s never got to do this to a girl before….let alone _see_ that much of a girl…  
  
….well...there was that one time--nope. Noooope, noooo-- let’s not think about that. _  
_ _  
_ Dean’s hands lifted from his sheets and moved to your cheeks, cupping them as he stared into your eyes for a moment. You still looked shocked that this was even happening, but he was starting to make you absolutely melt…  
  
One hand rose to tangle in your hair and then he dove down, firmly pressing his lips against yours and tilting his head. Your skin erupted in warmth and you dug your fingers into the back of his sweatshirt, gripping it tightly. Soft smacks and the faintest moans left both of your mouths, which Dean was unable to resist. He began to hump again, this time against you instead of his pillow.  
  
He couldn’t believe he was taking the lead on this. Dean acted completely on a split-second impulse, and somehow, it was working out. He wondered if you could feel his heart hammering against his chest.  
  
Dean’s humping caused your heart to skip a beat, and you weakly rose your legs to sort of half-wrap around his waist. Your mouths sloppily moved against each other-- looks like neither of you had a lot of kissing experience, but it still felt amazing nonetheless.  
  
Right as his tongue clumsily pressed against your lips and flicked around, your hands rose up a bit and you began tugging at his sweatshirt-- you were practically naked, while Dean was wearing _layers--_ he’d be burning up pretty soon if this got any further.  
  
“M-MMmmmm-mmhh--!!” Excited moans left him as he rose up from you just enough to let you lift his sweatshirt up, but he stretched to allow his mouth to remain connected to yours. Dean’s tongue slipped inside, the feeling causing a thick, warm pulse between your legs.  
  
Unfortunately for him, right as he began swirling his tongue inside your mouth he had to pull back to allow the sweatshirt to be lifted over his head. Dean panted a bit, and his hands took over as he removed the piece of clothing. Once it lightly hit the floor, he gazed down at you, and the two of you shared a brief moment.  
  
His lips parted ever so slightly, and he looked like he wanted to say something, but whatever thoughts he had evaporated when you sat up.  
  
Dean wanted to ask if this was okay-- if what he just _did_ was okay, but judging by your hands now working to unbutton his shirt--....he already knew your answer. _  
  
_

Sitting here and watching you undress him, his awkwardness set in, and the freckled boy merely peered down at you with a hazy and awestruck gaze as you worked your way up his shirt.  
  
You undid the final button, and reached up to slip his shirt off his shoulders.  
  
“Y-you’re--....really pretty--....” Dean dumbly breathed, watching you. Your _eyes_ , however, were raking up and down his scrawny pale chest. Without thinking, you leaned forwards and lightly pressed your lips to his skin. He shuddered immediately at the contact and bit his lip, feeling his hips twitch ever so slightly.  
  
Your soft... _soft_ lips softly smacked against his chest, and you were making Dean absolutely _weak_ ….not to mention his pants were getting uncomfortably tight. Each touch of your mouth against his skin felt like liquid sunlight, and the hot throbbing between his legs was growing difficult to ignore.  
  
Right as you reached his pectorals, Dean couldn’t hold himself back anymore, and his hands darted down to hastily unbuckle his pants. His hands were actually shaking a little.  
  
You gulped and slowly leaned back, allowing yourself a nice view as you continued to admire his bare chest, and the sight of the desperate teen in front of you frantically trying to get his pants off as fast as he could.  
  
It was pretty obvious what was coming.  
  
  
“D-do--...” You began, before clearing your throat-- your voice cracked a bit, and Dean completely froze in his tracks. His gaze met yours.  
  
“Do you have-- …..uh--....”  
  
  
Recognition flashed in his eyes, and the freckled boy enthusiastically nodded, looking back down to his pants. He undid the zipper and shimmied his hips out of his jeans, granting you a _nice_ view of his boxers and tent.  
  
He was-- ...woah. Okay--.....bigger than you thought he’d be--  
  
Not that you were expecting him to be small because he was a nerd or something, you just---  
  
You were torn from your thoughts by the sound of crinkling cellophane, and looked up. Sure enough, Dean had a condom. ….for….some reason..  
  
  
He seemed to guess what you were thinking, and stuttered. “I-I didn’t assume-- ...I-I’ve been-- ...I always carry one around just incase, like, I wasn’t thinking--”  
  
  
Your hands reached behind your back, and you began undoing your bra, satisfied with his explanation.  
  
  
“N-not that I don’t think you’re pretty-- ...I-I mean, I… _.totally want this,_ I just don’t want you to--....”  
  
  
The clasp unhooked, and you carefully slipped the article of clothing off. Just like that, Dean went completely silent as if he spontaneously lost the ability to speak.  
  
Which, considering what he was looking at….he basically did.  
  
The tent in his boxers actually twitched a bit.  
  
A soft cuss left Dean’s lips, and he stared at your chest hungrily. Feeling a sense of smugness, you leaned back onto the mattress and spread your legs. Dean gulped loudly.  
  
He quickly shimmied out of the rest of his jeans and kicked his socks and shoes off, feeling his heart hammer so heavily that he could actually see his chest pulsing slightly if he peered down. Every inch of his face was red, even up to his ears.  
  
Was this-- ….he was gonna--.....he was gonna actually lose his virginity here, wasn’t he?  
  
Were _you_ a--....?  
  
Dean turned back to you, and crawled on top of you on the mattress. You looked proud of yourself, but you’d be lying if you said you weren’t nervous either. Feeling his bare skin brush up against yours was absolutely intoxicating…  
  
He pressed his chest flush up against yours and returned to kissing your soft lips, shaking subtly in excitement and anticipation. Your textbooks and pencils were long abandoned on the floor to your left.  
  
Your hands wrapped around him and squeezed his back, feeling up more of his skin. They gradually traveled downwards, until they reached his small, flat ass.  
  
Dean may have had literally _no ass_ but that didn’t mean you didn’t like grabbing it. He squeaked and jumped slightly when you did so, letting out a high moan. Turns out he liked that a lot.  
  
You lightly smacked your palm against his rear once, twice, then traveled back up to grip the waistband of his boxers.  
  
_“M-Mm-mmhhh---.... O-ohh--...please….”_ He whispered ever so softly, bringing his hips forwards and gently grinding them against your thigh. You could feel his clothed hardness against your bare skin.  
  


“You sur--” You began, wanting to just..quadruple check, but--  
  
  
_“Yess yesyesyes--- pleaasseeee!”_ Dean whined out, grinding his bulge a bit more firm against you. A whimperish moan left your throat, and you wriggled as the throbbing between your legs was reaching a fevered pitch.  
  
When you finally began pulling his boxers down, Dean let out several quiet moans and sighs as his bulge twitched and throbbed with need. You’d barely done anything yet-- _how worked up did you get him?_ _  
_  
It was worth noting that you had never… _.seen_ a guy before, so when you finally pulled his boxers down past his crotch, your heart leapt in your chest. He was...definitely bigger than average, and holy shit was he hard.  
  
Dean was in a similar situation...he glanced away and felt his cheeks grow even hotter as you exposed him. Was he good enough…? He didn’t gross you out, did he?  
  
On impulse, you gently brought a hand forwards and rubbed the pad of your thumb against his tip. He inhaled sharply and his hips twitched as your touch sent sparks throughout his body. You were just testing the waters, but he seemed to like that a _lot._  
  
“M-M-Mmhhhh---!!” He whimpered out, and whispered your name, causing your heart to flutter in your chest. You kept going and rubbed gentle circles against his sensitive head. Subtly, his hips pushed forwards as his body hungered for more. You pressed your thumb down a bit firmer, smiling a bit as you enjoyed Dean’s soft, breathy cries.  
  
A shaky hand reached down and gently gripped the waistband of your panties. You rose your hips into his touch and slipped your hand down further, now trailing your fingertips up and down Dean’s shaft. You could faintly feel his cock pulsing beneath your fingers. His name left your lips in a pleading whisper, and his grip on your underwear tightened.  
  
After a brief pause, he slowly began pulling them down. Your guts wiggled in anticipation, and a few whimpers left you as you wriggled and lifted your hips to help.  
  
This was it...you were finally going to punch your v-card with a guy you basically just met today. Though Dean was...insanely cute, and getting you turned on as fuck. You peered up at him, and your heart fluttered again at what you saw.  
  
He was staring down at your panties intensely as he slowly pulled them down, with his gaze sparking with a hint of nervousness. They finally slipped down your hips, and you rose your legs to help him pull them off completely.  
  
Completely bare, it was your turn to look away in embarrassment and feel your skin bloom into heat as Dean’s gaze traveled up and down your entire form.  
  
  
“O-Oohh-- ...oh wow….” He muttered, softly. Dean slowly lowered himself back down on top of you, and cupped your cheeks. His thumbs softly brushed against your skin.  
  
  
“H-hey-- ..I’ve never done this before, so…” You began, unable to meet his gaze. His expression sobered up just a bit, and he sat up a little.  
  
  
“I-It’s okay, I haven’t either. So-- ...uh-- ….I’ll be careful.” Dean assured, giving you a soft, nervous smile. His gaze briefly drifted back down to your folds, before he sat up fully. He turned away from you and worked to rip open the condom.  
  
  
He rolled the condom up his shaft, and you spread your legs a little, getting into position. When he turned back, his heart pounded at the sight of you. Dean gulped and returned to hovering over you. You both looked nervous.  
  
Dean looked down and gripped the base of his cock, aiming himself, and you felt a wave of arousal when you finally felt his tip press up against your entrance. He hesitated for a moment, before gently beginning to slip inside. It took a bit of effort to get his tip inside of you, though once he pushed it in, the rest of his shaft entered you easier.  
  
You tensed up and found yourself holding your breath, biting your lip and glancing away. The feeling of something slipping inside you like that was entirely foreign, yet every inch deeper he reached just made you want more. Once Dean’s cock made it halfway inside you, soft groans left your lips as you rose your hips again to make his entrance easier.  
  
He was shaking almost, trying to keep himself together as he slowly slipped inside, feeling all of this for the first time. Although he was wearing a condom, the wet, warm, _tight_ sensations of your walls squeezing and adjusting to his length were almost addicting. His body cried out for more, though he controlled himself-- he’d never forgive himself if he hurt you...as far as you were concerned, you were made out of glass.  
  
  
“M-Mh-- ...o-....o-ow-- ….D-Dean, hold up-- ..aaaahh---” You hissed and whimpered, feeling your thighs quiver..at first your walls could keep up and adjust to his length, but he was almost fully in and you needed a quick breather.  
  
  
Dean did a double-take as he fully hilted inside of you, and felt a wave of horror as he saw your pained expression. You heard him suck in a frightened breath.  
  
  
“--!! O-ooh-- ...I-I’m sorry, I didn’t hurt you, did I?”  
  
  
“N-not really-- ..you’re just-- ….mmh-- …..k-kinda big….” You explained, tense beneath him as the sharp stinging between your legs slowwwly faded away. Dean blinked down at you, completely dumbstruck.  
  
  
“--...I-....I am?”  
  
  
You nodded, screwing your eyes shut, before exhaling slowly. The boy on top of you waited anxiously. “--....o-okay, I think I’m good.”  
  
  
“A-are you sure?”  
  
  
“Yeah.”  
  
  
Dean took a moment to try and calm down..his heart had been beating alarmingly fast since he first pounced on you. He gulped and pressed his palms into the sheets on either side of your head, digging his fingers into the cloth. You felt a bit boxed in and pinned down by him, which a part of you….really liked…  
  
A soft gasp left your lips as you felt him slowly pulling back, his shaft brushing up against your walls. Dean pushed back in softly and waited half a second, making sure that didn’t hurt you, before repeating it again…  
  
...and then again…  
  
And again…  
  
He was slowly working himself into a rhythm, and the tension and stinging pain quickly began to melt away, replaced with a growing climbing feeling. Every thrust left you wanting more…  
  
  
“F-faster-- ….f-fuck-- ...D-Dean--...”  
  
  
His grip on his sheets tightened, and Dean cutely bit his bottom lip as his rhythm sped up just a bit. Ever so softly, the bed beneath you two was beginning to shake. Each of his thrusts was causing you to shift under him, and you wriggled as the pleasure built up.  
  
  
“M-Mmhh---! A--..A-Aahh--....” You squeaked and turned your head away as you felt a coil within you tightening up.. Dean lowered himself down so his chest was flush against yours, and his palms left their position of gripping the sheets. His thrusts briefly grew just a touch erratic as Dean groped around for your hands.  
  
He softly squeezed your wrists, before pinning them down to where his hands were just a few moments ago: on either side of your head. A wave of arousal coursed through you as Dean pinned you down. “F-Fuck-- ...fuck…..”  
  
Dean sped up again, and his thrusting grew rougher as your noises drove him further and further into a lusty haze. A few breathy groans would leave him as he started to pound you. His movements were causing the bed to start to _creak_ in addition to shake, and you arched your back.  
  
  
“A-AAahh--!! M-More, please-- _...f-fuck--...”_ _  
_  
  
He squeezed your hands and did as you asked, wanting to go harder regardless..his eyes squeezed shut, and a few moans slipped through his lips as he focused on the noises...his skin slapping against yours, the sheets shifting around as you wriggled, your overwhelmed squeaks and moans, the sound of the bed creaking from his thrusting..  
  
  
“A-Aahhg-- ….o-oohhh--....Mmhh…” Dean’s features twisted a bit, and his brows furrowed as he got even further into fucking you. This felt so good...everything felt so fucking good… His arms faintly shook and quaked as he had to fight back the urge to just cum immediately. Dean didn’t want this to end that fast...for either of your sakes..  
  
  
“D-Dean-- ...m-mmhh-- ...f-fuck me--”  
  
  
His heart nearly leapt out of his chest.  
  
  
“F-fuck me--!! F-fuck me-- ….h-harder, I need it harder--”  
  
  
He buried his face into your neck and smothered it in kisses and bites, groaning as Dean refused to hold back any longer-- you obviously didn’t want him to. Dean’s hips roughly slammed against yours as he rammed his cock in and out of you, pulling a loud cry from your lips.  
  
  
“A-AAH--!! O-oh fuck--”  
  
  
The bed rocked intensely beneath you, and your walls fluttered as you heard the headboard start to bang against the wall. Your coil was tightening, and Dean groaned desperately against your neck as he felt how turned on you were getting. He bit roughly at your soft skin and sucked, only thrusting harder and harder. God, he wanted to fuck your brains out…  
  
  
“M-Mmhhh-- ….f-fuck--....f-fucking take it…!” Dean breathed out, grinning faintly. Your walls tightened around his cock for a moment, and he almost choked on air.  
  
  
“Y-yyeah-- ..yeah--!! O-Ohh--...h-hhhaahh-- …” You arched your back, doing anything to get him in deeper. He was thrusting at a quick and brutal pace by this point, and the sounds of the bed creaking, rocking back and forth, and the headboard slamming against the wall were almost drowning out your moans and slapping noises.  
  
  
Dean kept at that pace-- honestly, he didn’t think he could go any rougher, and kept marking up your neck. He couldn’t believe he was doing any of this...losing his virginity and having such rough sex with a girl that he could hear the bed creaking and rocking..  
  
  
“H-hhh-h-haahh--!! O-Ooohh-- ..ff-ffuck, this is so good--...!!” Dean cried out in ecstasy, pulling back to moan as he pounded you. “I--....a-are you close-- …? I-I’m gonna---!”  
  
  
You suddenly squeezed your thighs around Dean’s waist and began rocking your hips against his, crying out as his thrusts were making your head spin. His question was soon answered as your walls suddenly clamped down on his shaft, and a warm wetness gushed from your pussy. Dean gasped, and his next few thrusts were exceptionally rough, though erratic…the feeling of you cumming on his cock was--  
  
  
“F-FFuck--!! I-I’m cumming-- ...A-A-Aaahhh---!” Dean groooaaaned out as he came inside you, shuddering and squeezing your hands tightly as he finished with you. His thrusts slowly died down and grew softer as his moans faded into pants and gasps.  
  
You were entirely limp and feeling like a bowl of jello beneath him, and let out a soft ‘guh’ as Dean collapsed on top of you and worked to catch his breath..you could feel his scrawny chest against your bare skin heaving for air. You both were covered in sweat, and red from head to toe.  
  
  
“H-...h-holy shit…” You breathed quietly, gazing up at the ceiling as you hadn’t quite come down from your high yet. Dean was still catching his breath, though one of his hands pulled away from yours and drifted upwards to weakly play with your hair.  
  
You were nervous before, but honestly...that was fucking amazing. Dean could take your virginity _anytime._  
  
...well..he couldn’t anymore, because he just did and you really only get one shot at that, but--  
  
It was good. It was fucking great and you’d totally do it--him-- again.  
  
Dean curled some of your hair around his finger and gazed down at you with a drunk expression, still waist-deep in the afterglow. “I love you…..” He breathed, gently.  
  
  
You both froze. Dean tensed up.  
  
  
“Your-- …..hair-- ...I love your hair. It...smells like strawberries…” He quickly attempted to correct, before taking a whiff of your locks. Dean sighed dramatically.  
  
  
You felt bad. You didn’t even make the flub up and _you_ felt embarrassed. But….y’know, he was super cute...so you found yourself not too bothered by it.  
  
Dean slowwwly pulled out of you, and you both shuddered as his shaft brushed up against your walls again...after cumming, both of you were insanely sensitive. As you slowly drifted down from the afterglow, Dean sat up and turned away as he disposed of the condom.  
  
Similar thoughts flowed through both of your heads. Was this gonna be just a one time thing? Neither of you wanted that… It may have just been the hormones, but Dean already felt kind of attached to you.  
  
  
“S-So, uh--”  
  
  
“H-Hey, did you--” You both spoke up at the same time, after Dean tossed the condom in the trash. You froze, then he giggled nervously and rubbed the back of his neck.  
  
  
“You first?”  
  
  
“--...did you..like-- ...wanna make this a thing?”  
  
  
Dean paused, and felt his heart doing flip flops. Were you...asking what he thought you were asking? “U-Uh-- ...y-...yeah, actually..! I’d-- ...I’d really like that…” He smiled shyly, and mused a few fingers through his slanted bangs. As he glanced away, you sat up and began redressing.  
  
  
“Good, ‘cause I kinda think you need it.” You smiled at him, and slipped your underwear on. His flustered giggles continued, and the boy hunched forwards a bit.  
  
  
God he was skinny as fuck but _so fucking cute._ _  
_ _  
_ Once you were dressed, you gathered up your books and straightened your hair..even though everyone in the entire hallway could have probably heard what just happened, you didn’t want to walk out of Dean’s dorm with _total_ sex hair.  
  
He pulled his boxers back on, and watched as you stood back up. You were leaving so soon…?  
  
  
“Anyway, this was--....really, really nice, but I’ve got-- ….homework I-- ….need to…--”  
  
  
You trailed off as Dean approached you, and cupped your cheek. He leaned in, and your eyes fluttered closed. He didn’t want to let you leave without sneaking in one last kiss.  
  
You melted into his kiss and tilted your head, and Dean followed suit, slipping his tongue into your mouth again and gently swirling it around. Right as you were about to start kissing him back, Dean pulled back.  
  
  
“--....h-....have a nice night…” He whispered softly, his breath fanning against your face and giving you goosebumps.  
  
  
After a moment, you finally came out of your haze and nodded. “Y-....yeah. G-G’night, Dean.” You smiled lopsidedly and opened the door just a crack before squeezing through, not wanting to give the entire dorm a view of Dean’s half naked body.  
  
As you walked down the hall, the freckled boy slowly clicked the door shut-- rather, he tried to, before a foot jammed itself between the door and the frame. The owner of said foot hissed.  
  
  
“W-Whuh--?” Dean opened it further, and paled when he saw who it was. They paled as well.  
  
  
“YOU were making all that noise?!” Jared spluttered in disbelief, causing heat to bloom onto Dean’s cheeks. He whispered for his roommate to keep his voice down, then yanked him inside and shut the door.  
  
  
You heard the exchange behind you and tried to hide a snicker, though failed, and wheezed as you made a turn and headed towards the entrance to the boy’s dorms.  
  
Yeah, you definitely wanted to see him again.  


**Author's Note:**

> AAAAAAHAHAHA HERE IT IS
> 
> oh my god this took me weeks but it's finally done! honestly i have a LOT more fun writing hank, but i absolutely needed to bring this thing into existence so I could smooch my boy
> 
> AND NOW ALL OF YOU CAN, TOO
> 
> coming up eventually is:
> 
> reader/shaggy haired hank
> 
> a multi-chapter fic taking place immediately after season 7 with reader and an obsessive bathank ( this one is gonna take awhile bc i actually need to write a STORY )
> 
> reader/hank n' dean sandwich
> 
> I wanna write more dean ones, though I might be focusing on earlier seasons since season 7 is kind of an-- ...well it sucks
> 
> the ending sucks
> 
> i'm deleting it


End file.
